# US 2014/0155484 A1 · Method of treating liver disorders

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- Number: US 2014/0155484 A1
- Document ID: US20140155484A1
- Status: Published application
- Kind: A1
- Application number: 14/152,924
- Filed: 2014-01-10
- Published: 2014-06-05
- Earliest claimed: 2012-12-05
- Assignees: MediciNova, Inc.
- Applicants: MediciNova, Inc.
- Inventors: Kazuko MATSUDA
- Web page: https://patentgrep.com/patent/US20140155484A1

## CPC

- A61K 31/192: having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid {(cannabinoids A61K31/658)}
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound of Formula (I): or a metabolite thereof, or an ester of the compound of Formula (I) or the metabolite thereof, or a pharmaceutically acceptable salt of each thereof, wherein m, n, X1 and X2 are as defined herein, is useful for inhibiting liver steatosis, lobular inflammation, hepatic ballooning and hepatic scarring.

## Claims

### Claim 1

A method of inhibiting steatosis in a patient suffering therefrom comprising administering to the patient in need thereof an effective amount of a compound of Formula (I):
or a metabolite thereof, or an ester of the compound of Formula (I) or the metabolite thereof, or a pharmaceutically acceptable salt of each thereof, wherein m is an integer from 2 to 5, and n is an integer from 3 to 8, X1 and X2 each independently represent a sulfur atom, oxygen atom, sulfinyl group or a sulfonyl group, provided that X1 and X2 are not simultaneously oxygen atom.

### Claim 2 (depends on 1)

The method of claim 1, in which the compound of Formula (I) is of Formula (IA)

### Claim 3 (depends on 1)

The method of claim 1, in which the metabolite of the compound of Formula (I) is a compound of Formula (IB):

### Claim 4 (depends on 1)

The method of claim 1, in which the compound is administered orally.

### Claim 5 (depends on 4)

The method of claim 4, in which the compound is administered as a tablet or a capsule.

### Claim 6 (depends on 2)

The method of claim 2, in which the compound is present in an orthorhombic polymorphic form A that is substantially free of other polymorphic forms.

### Claim 7 (depends on 1)

The method of claim 1, in which the compound is administered as a liquid dosage form.

### Claim 8 (depends on 1)

The method of claim 1, in which the compound is administered in an amount from 100 to 4,000 mg/day, divided into one, two, or three portions.

### Claim 9

A method of inhibiting lobular inflammation in a patient suffering therefrom comprising administering to the patient in need thereof an effective amount of a compound of Formula (I):
or a metabolite thereof, or an ester of the compound of Formula (I) or the metabolite thereof, or a pharmaceutically acceptable salt of each thereof, wherein m is an integer from 2 to 5, and n is an integer from 3 to 8, X1 and X2 each independently represent a sulfur atom, oxygen atom, sulfinyl group or a sulfonyl group, provided that X1 and X2 are not simultaneously oxygen atom.

### Claim 10 (depends on 9)

The method of claim 9, in which the compound of Formula (I) is of Formula (IA)

### Claim 11 (depends on 9)

The method of claim 9, in which the metabolite of the compound of Formula (I) is a compound of Formula (IB):

### Claim 12 (depends on 9)

The method of claim 9, in which the compound is administered orally.

### Claim 13 (depends on 12)

The method of claim 12, in which the compound is administered as a tablet or a capsule.

### Claim 14 (depends on 10)

The method of claim 10, in which the compound is present in an orthorhombic polymorphic form A that is substantially free of other polymorphic forms.

### Claim 15 (depends on 9)

The method of claim 9, in which the compound is administered as a liquid dosage form.

### Claim 16 (depends on 9)

The method of claim 9, in which the compound is administered in an amount from 100 to 4,000 mg/day, divided into one, two, or three portions.

### Claim 17

A method of inhibiting hepatic ballooning in a patient suffering therefrom comprising administering to the patient in need thereof an effective amount of a compound of Formula (I):
or a metabolite thereof, or an ester of the compound of Formula (I) or the metabolite thereof, or a pharmaceutically acceptable salt of each thereof, wherein m is an integer from 2 to 5, and n is an integer from 3 to 8, X1 and X2 each independently represent a sulfur atom, oxygen atom, sulfinyl group or a sulfonyl group, provided that X1 and X2 are not simultaneously oxygen atom.

### Claim 18 (depends on 17)

The method of claim 17, in which the compound of Formula (I) is of Formula (IA)

### Claim 19 (depends on 17)

The method of claim 17, in which the metabolite of the compound of Formula (I) is a compound of Formula (IB):

### Claim 20 (depends on 17)

The method of claim 17, in which the compound is administered orally.

### Claim 21 (depends on 20)

The method of claim 20, in which the compound is administered as a tablet or a capsule.

### Claim 22 (depends on 18)

The method of claim 18, in which the compound is present in an orthorhombic polymorphic form A that is substantially free of other polymorphic forms.

### Claim 23 (depends on 17)

The method of claim 17, in which the compound is administered as a liquid dosage form.

### Claim 24 (depends on 17)

The method of claim 17, in which the compound is administered in an amount from 100 to 4,000 mg/day, divided into one, two, or three portions.

### Claim 25

A method of inhibiting hepatic scarring in a patient suffering therefrom comprising administering to the patient in need thereof an effective amount of a compound of Formula (I):
or a metabolite thereof, or an ester of the compound of Formula (I) or the metabolite thereof, or a pharmaceutically acceptable salt of each thereof, wherein m is an integer from 2 to 5, and n is an integer from 3 to 8, X1 and X2 each independently represent a sulfur atom, oxygen atom, sulfinyl group or a sulfonyl group, provided that X1 and X2 are not simultaneously oxygen atom.

### Claim 26 (depends on 25)

The method of claim 25, in which the compound of Formula (I) is of Formula (IA)

### Claim 27 (depends on 25)

The method of claim 25, in which the metabolite of the compound of Formula (I) is a compound of Formula (IB):

### Claim 28 (depends on 25)

The method of claim 25, in which the compound is administered orally.

### Claim 29 (depends on 28)

The method of claim 28, in which the compound is administered as a tablet or a capsule.

### Claim 30 (depends on 26)

The method of claim 26, in which the compound is present in an orthorhombic polymorphic form A that is substantially free of other polymorphic forms.

### Claim 31 (depends on 25)

The method of claim 25, in which the compound is administered as a liquid dosage form.

### Claim 32 (depends on 25)

The method of claim 25, in which the compound is administered in an amount from 100 to 4,000 mg/day, divided into one, two, or three portions.

### Claim 33

A method of reducing and/or inhibiting elevated liver hydroxyproline levels in a patient suffering therefrom comprising administering to the patient in need thereof an effective amount of a compound of Formula (I):
or a metabolite thereof, or an ester of the compound of Formula (I) or the metabolite thereof, or a pharmaceutically acceptable salt of each thereof, wherein m is an integer from 2 to 5, and n is an integer from 3 to 8, X1 and X2 each independently represent a sulfur atom, oxygen atom, sulfinyl group or a sulfonyl group, provided that X1 and X2 are not simultaneously oxygen atom.

### Claim 34 (depends on 33)

The method of claim 33, in which the compound of Formula (I) is of Formula (IA)

### Claim 35 (depends on 33)

The method of claim 33, in which the metabolite of the compound of Formula (I) is a compound of Formula (IB):

### Claim 36 (depends on 33)

The method of claim 33, in which the compound is administered orally.

### Claim 37 (depends on 36)

The method of claim 36, in which the compound is administered as a tablet or a capsule.

### Claim 38 (depends on 34)

The method of claim 34, in which the compound is present in an orthorhombic polymorphic form A that is substantially free of other polymorphic forms.

### Claim 39 (depends on 33)

The method of claim 33, in which the compound is administered as a liquid dosage form.

### Claim 40 (depends on 33)

The method of claim 33, in which the compound is administered in an amount from 100 to 4,000 mg/day, divided into one, two, or three portions.